Trifluoroacetic acid → HCID 57568671, compound

HRID 1845717Notes

Reaction equation

HRID 1845717 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:35][O:36][CH2:37][CH3:38])[N:14]([CH2:15][C:16]([NH:19][C:20](=[O:34])[CH2:21][CH2:22][C:23]([NH:25][NH:26]C(OC(C)(C)C)=O)=[O:24])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:35][O:36][CH2:37][CH3:38])[N:14]([CH2:15][C:16]([NH:19][C:20](=[O:34])[CH2:21][CH2:22][C:23]([NH:25][NH2:26])=[O:24])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68923284HCID 68923284, compound

Product 1

HCID 57568671HCID 57568671, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 2-[4-({2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}amino)-4-oxobutanoyl]hydrazinecarboxylate (792 mg, 1.50 mmol) in dichloromethane (30 mL) was treated with trifluoroacetic acid (3 mL). After stirring for 2 hours, additional trifluoroacetic acid (3 mL) was added to the reaction mixture and stirring was continued for 1 hour. The reaction mixture was concentrated under reduced pressure and the resulting syrup was dissolved in water. The solution was made basic by the addition of concentrated ammonium hydroxide and then was extracted repeatedly with 10% methanol/chloroform. The combined organic portions were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude white solid was purified by chromatography on silica gel (gradient elution, 25%-75% CMA in chloroform) gave 340 mg of N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-4-hydrazino-4-oxobutanamide.

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe resulting syrup was dissolved in water
  5. additionThe solution was made basic by the addition of concentrated ammonium hydroxide
  6. extractionwas extracted repeatedly with 10% methanol/chloroform
  7. dry with materialThe combined organic portions were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude white solid was purified by chromatography on silica gel (gradient elution, 25%-75% CMA in chloroform)

Sources & evidence

ORD record
ord-024a38d4f8df407aaf91c71d9d6a9578
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

Loading…